Eating a Desert Full of Broken Glass: 8 Lessons for Finishing Never-Ending, Soul-Crushing Projects When You're Burned Out and Can't Lift a Finger Anymore.

This is not a conventional guide to productivity or project management.

Deep Work, Getting Things Done, and the like assume that you’re healthy, aligned with your project, and still have energy left.

But what about when the gears grind to a halt? When you're crushed between "I have to get this done" and "I don't have an ounce of energy left to give?" When the goal posts keep moving and you beg your body/brain for "just a little more," but they respond with a silent middle finger.

What do you do when your health starts failing under the stress?

For the four years it took to sell my company, this was my mental home. I describe it as being stuck in a desert full of broken glass, having to eat my way out. I'm still periodically amazed that I did, and that this is the same lifetime.

Here's what I can tell you from the other side -

1. There is a wonderful, comparatively harmonious life waiting for you at the end of this piece-of-shit project.
2. The longer you stay in this shit hole, the more damage you do to yourself, the longer it'll likely take to recover. Although life is better, I am still paying the price. Navigate as gracefully as possible, but do not get comfy here. Do not rationalize why an additional month, year, or era is ok. This is slow-motion suicide. Get out as efficiently as possible.
3. The lessons below cost me more than I wanted to pay. The only way I can justify that price is by sharing them with you. Steal them. Get out and move on. Live a beautiful life. 
   
   There is no reward for doing this the hard way.

With that said, let's get you out. Let's get you free.

Here are my lessons for eating your way through a desert full of broken glass.

1. Clarify Your Intentions For the Project Now
2. Lighten the Load. Find the Effort-less Way.
3. Quit.
4. Or Decide to Stick
5. If You Stick, Sign a New Contract & Define Done.
6. Forget Heroic Sprints. Build the Atomic Habit of Showing Up.
7. Get Out of the Closet. Create a Conspiracy Around Your Success.
8. Reframe the Opportunity to Finish

(Roughly in order. Individually complete.)

Lesson 1: Clarify Your Intentions For the Project Now

Before any productivity hacks, before you decide to stick or quit, ask a more important question:

What job did I give this project in my life?
More specifically, what are my intentions for it now?

We get pulled into projects by momentum, short-sighted desires, social pressures, and countless other poorly defined reasons. Sometimes, we do have intentions, but they shift in transit.

That's ok. You're allowed to grow and change your mind.

So, what are your intentions for this project now?

A friend of mine, inspired by the newest vibe-coding tools, spent several months coding an app. Three months in, life got in the way. Now, he's wrestling internally, "Do I push this to the finish line, or do I let it go?"

But this question is premature.

What's his intention?

If it's to follow his curiosity, explore new technologies, and get his hands dirty after years of managing instead of building, then he’s already succeeded. The project has already done its job. He can confidently wrap it up and move on.

If, on the other hand, his intention is to ship something into the world and get paying customers, then he’s not done yet. To fulfill that intention, he needs to ship.

Different intentions. Different answers.

And, if you're reading this, I'd bet that your primary intention for this project at this point is to be done. This is important clarity.

Regardless, once you clarify your intentions for this project now, there are 2 ways to proceed.

Lesson 2: Lighten the Load. Find the Effort-less Way. ¹

Whether you quit or stick with this project (Lessons 3 & 4, below), one thing is for sure - what you're doing isn't working. It's unsustainable, and that's why you're here now.

It's time to release your prior concept of the project and lighten the load.

You're likely making life more difficult by optimizing for a bunch of BS beyond your intentions. As a fellow optimizer, I know the pull towards "doing it right," getting the most money, making the best deal, etc. This is the pull towards moving goal posts and pushing Done ever further away.

It's time for your insecure, A+ neurotic to learn from the confident, C-student - dirty and done is better than ideal and never-ending.

You'll have plenty of opportunities to get style points and optimize elsewhere in life. Optimize when you’re enjoying yourself, or at least not getting killed.

Right now, lighten the load and find the easy way to Done.

Liberate yourself from the tyranny of optimal and embrace the gift of “good enough."

Questions to ask

• Can you simplify your intentions? What is your essentialintent?
• What is the most essential version you can ship to satisfy your intention? Are there any criteria you can strip?
• What’s the absolute minimum viable way? What’s stopping you from taking it? What do you need to give yourself permission to do so?
• Can this be easier?
• Is there a version of this that can be fun?

Don't worry. You don't have to commit to anything yet. I'm just asking you to find the effortless way. Once you do, there's an even more efficient path to Done.

Lesson 3: Quit. ²

Now that you've clarified the purpose of this project in your life, and you have a concept of a less painful way forward, decide -

• Am I going to see this through?
• Or, is there a graceful way to quit and move on with my life?

Simply put, if your intention is to be done, quitting is likely the most efficient way there.

But what about the shame? The cognitive dissonance? The lectures from parents and coaches?

Don't winners never quit and quitters never win?!

No. That is patently false.

At the risk of becoming a broken record, remember:

We must quit the trivial many to grit through the essential few.

Effective quitting is not failure.

It is one of the most important, underdeveloped skills for success.

Warren Buffett didn't fail when he shut down Berkshire's textile operations. Jeff Bezos didn't fail when he left Wall Street. Michael Jordan didn't fail when he quit baseball for basketball - both times.

By contrast, Muhammad Ali likely failed by sticking around 5 years past his prime, accumulating irreversible brain damage for his efforts. I got a broken thyroid + some other goodies for mine.

Nearly every story of sustained, exceptional success is a story of deliberately quitting the merely good for truly great.

You are not the things you used to do.
You are not the roles you used to play.
Your value is not the projects of your past.
You have the right and responsibility to move on.

So that's it. Quit. Bye!

Lesson 4: Decide to Stick.

Oh, you're still here?

Looks like I didn't convince you to quit.

If you're not quitting, you're deciding to stick.

At the risk of that sounding too obvious, allow me to repeat -

You are deciding to stick with this.

You know what that means, right?

You're not a victim.

You're not oppressed.

You're making a conscious decision to pursue an opportunity, not conceding to a punishment.

Any time you start speaking to yourself in victim language, you'll come back here and remember that this journey is an act of agency. You don't have to. You get to do this.

This means you can begin cultivating gratitude for your situation. For the opportunity to achieve whatever you're trying to achieve. For the strength to do the work. For the wisdom to pursue the most efficient, effortless route.

Yes, you'll struggle. But you'll do so congruently.

It won't make it easy. But it'll make it tolerable. And that helps.

"But I don't have a choice."

You absolutely have a choice.

You know how I know? Because you haven't quit. You believe that the consequences of not doing it are worse than the pain of doing it. Can you imagine a world where you're powerless and you don't even have the opportunity to do this shitty project? In that world, you're just dealt the worst possible outcome, no questions asked.

Good news. You don't live in that world.

So own your choice. Always. 
You can quit with dignity. But don't stick pathetically.

Lesson 5: If You Stick, Sign a New Contract & Define Done. ³

Your brain's first job is to protect you, not to realize your potential. Historically, it is more important not to get eaten by a lion than to write the great American novel or to achieve product-market fit.

Thus far, you've demonstrated that you're willing to work "as hard as you have to, for as long as it takes." From your brain's perspective, this is indistinguishable from signing up for a lifetime of misery or marching slowly toward your death. Like a boss who repeatedly asks for exceptional effort in exchange for rewards that never come, your subconscious learns, "This is bullshit, I'm getting screwed." Eventually, it pulls the plug on productivity.

It protects you from your own negligence.

“I don’t trust you anymore.”

Your subconscious understands this simple truth -

Life is limited.
And nothing is worth doing forever.
Especially if it's not working.

But we can get ourselves to do inordinately hard things - show up when tired, run marathons, endure med school.

How?

By making contracts with ourselves - agreements with defined terms and clear endings. A marathoner can run 26.2 miles precisely because he knows there's a finish line. If there was no end in sight, he'd likely quit at first blister.

When we find ourselves pushing past a contract's terms or expiration date, our subconscious pulls the plug. This is the story of every midlife crisis. And it is likely the story of your current predicament.

So here's how you're going to rebuild trust with yourself. This is how you're going to get your subconscious back on board.

You're going to enter a new contract with yourself.

“I will render my services to this project, until X time, under Yconditions.”

KEY POINT: STATES & DATES

Contracts work when they have states and dates for termination.

What would have to be true, by what date, for you to either ship or pull the plug?

For example:

• “We will have a functional prototype by January 31, or we pull the plug on February 1, accepting sunk costs.”
• “If we don't get [KPI-of-choice] above 30% by end of 2026, we conclude that this problem is too hard/too expensive, return remaining capital to investors and let everyone pursuemore promising projects.”
• “If we don't have an acquisition offer by my 35th birthday, we stop all new projects, begin shutting down and liquidating assets.”

If you give your mind a believable vision of how this ends, it may just offer to help you get there.

But if all you offer is the same raw deal you always have, all pain, no gain, and no end in sight, you'll struggle to lift a finger. Every pound will feel like a ton.

A new contract won't make the work easy, but it'll get you moving again.

Once you can see the finish line again, with clear states and dates, it's time to get back to work.

Lesson 6: Forget Heroic Sprints. Build the Atomic Habit of Showing Up. ⁴

If you’re deeply burned out, forget heroic efforts. Forget massive daily progress.

This is not the time to listen to Tim Ferris and Elon about collapsing timelines (unless it's the part about getting rid of non-essentials, not the part about sleeping under your desk).

I know you want to finish, just like a marathoner wants to hit 26.2 miles, but successful marathoners don't fixate on the finish line, they focus on putting 1 foot in front of the other, over and over again.

That's your job. Show up every day and put one foot in front of the other, nothing more.

What is the smallest conceivable unit of daily progress that is almost impossible to fail at?

It may feel silly or embarrassing to admit. That's fine, as long as it's doable on your worst day.

When I was selling my company, that meant opening the relevant project management file. To write this essay, I listened to my last version before writing anything. When I go to the gym, I do my 2-minute warm-up, no weights involved.

You may aspire to do four 90-minute deep work sessions, but that is precisely an aspiration. It won't happen every day. That is not failure. It's reality.

What you do not deviate from is your atomic habit of showing up. You don't put up zeros.

And if you do miss? You accept, forgive yourself, and commit to not failing 2 days in a row.

This is how you eat your way out of a desert full of broken glass - 1 mouthful at a time.

Lesson 7: Get Out of the Closet. Create a Conspiracy Around Your Success ⁵

James Clear, author of Atomic Habits, said that the most overlooked lesson in behavior change is this:

If you want a behavior to become a major part of your life, join [or create] a culture where that behavior is the norm.

We are tribal animals and few things shape behavior more reliably than the engaged presence of others. Whether a coach, mentor, professional group, board, your co-founders, or management team — showing up and getting shit done becomes easier when you're not working in a closet.

This may feel unintuitive right now because you feel like you're doing a shit job, and the last thing you want is to draw attention to yourself. A common, sensible defense mechanism is to isolate and suffer in private. But besides this being the path of most pain, it's also the path of even shittier progress.

When I was struggling to lift a finger on exit work, I set up a weekly status meeting with my co-founders (who are also my parents) where I had to explain what got done, what's next, and what's in the way. Normally, managers use these meetings to keep tabs on subordinates. I was using it to get performance out of myself.

And it worked.

Progress became a team sport, even if I was the only one working on it.

Four long years later, one foot in front of the other, we finally sold.

Create or join a structure where others expect you to make progress.

As long as there is one person who holds that frame, you will not languish in private. You will benefit from a conspiracy around your success.

Lesson 8: Reframe the Opportunity to Finish ⁶

Here is your current frame:

• Fuck this fucking bullshit, I just want to be done with this shit already.

Here is a more graceful and effective frame that helped me:

• In almost every important undertaking, you should expect the most difficult hurdles at the end, when you're most depleted and tired. In these moments, you can either find a way out (which, per Lesson 3, is sometimes the right move) or a way through. There are not many opportunities to run the last mile, so you can embrace this one to develop the skill of finishing.

Buying my first home was brutal. I didn’t know what I didn’t know, and life kept reminding me - violently.

When my offer was finally accepted, they sent me 400 pages of documents. It felt like getting punched in the face 1 mile short of the finish line.

After the rage passed, I realized I was stuck in the first frame, while the second was available to me.

I didn’t want to become the guy who lamented everything he almost did, until someone inevitably screwed him. I wanted to train my brain for the next time - when the stakes would be higher.

So I calmed down and found a way through.

This experience echoed in my head every time a new hurdle appeared in my exit process, each a new opportunity to finish running the last mile.

Reframe the struggle of the present as a gift to your future self. Just don't use it as an excuse to stay in the desert any longer than necessary.

How to Eat Your Way Through a Desert Full of Broken Glass

1. Clarify Your Intentions For the Project Now
2. Lighten the Load. Find the Effort-less Way.
3. Quit.
4. Or Decide to Stick
5. If You Stick, Sign a New Contract & Define Done.
6. Forget Heroic Sprints. Build the Atomic Habit of Showing Up.
7. Get Out of the Closet. Create a Conspiracy Around Your Success.
8. Reframe the Opportunity to Finish

None of this will make it easy.

But it will move you towards the promised land -  Done.

Further Reading & Credits

¹ The quintessential books on essentialism and effortlessness are Greg McKeown's Essentialism and Effortless . They were life coaches I returned to almost monthly during my exit journey.

Effortless is my "I know what to do, but it's too hard, too much, and I can't breathe" book. Essentialism is my "nothing makes sense, the world feels too big, I'm lost at sea" book.

² Decision scientist Annie Duke wrote the quintessential book on quitting, aptly titled Quit. It is one of my most recommended and thanked for books of the past few years. It was invaluable for my own sanity through my exit process. If you're reading this, you owe it to yourself to read it as well.

³ Dale Diaz coached me in my 20s and taught me about contracting. I've found it profoundly helpful and little discussed elsewhere. "States and dates" is straight out of Quit, but maps perfectly onto Dale's teachings.

⁴ Atomizing giant projects & developing the habit of showing up are insights I had from reading Atomic Habits 100+ times. Your behavior is a project that is both always and never done. Rereading recommended.

⁵ For the highest-leverage tool in the behavior change toolbox, read essay #15 in this series. "I Read Atomic Habits >100 Times, Built a 5-Year Gym Habit, Sold a Company. If There's an Ultimate Method of Behavior Change, This is It (Supported by James Clear)" (🔗 IG, X, LI)

⁶ Reframing is natural, but Scott Adams' Reframe Your Brain made me appreciate the full power of this tool. The return on effort is outrageous.